A lake surrounded by trees with autumn leaves.

Holiday Homes in Oakland

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oakland holiday homes

A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

1. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (17 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is AU$355
includes taxes & fees
28 Sept - 29 Sept
Discover Oakland charm near Colby College 10 min
A wooden deck with outdoor furniture, a large potted plant, and string lights.

2. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, Exceptional, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
The price is AU$518
includes taxes & fees
28 Sept - 29 Sept
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A modern building with a black exterior and a large glass entrance.

3. Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.4 out of 10, Exceptional, (9 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is AU$209
includes taxes & fees
29 Sept - 30 Sept
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A house with a white front door, a wreath, and flower boxes on the windowsills.

4. Arden Cottage

Arden Cottage
Mount Vernon
The price is AU$602
includes taxes & fees
25 Oct - 26 Oct
Arden Cottage
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

5. A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.
New Sharon
10.0 out of 10, Exceptional, (30 reviews)
"Loved the cabin and the view!! Had a great stay, thank you to our host!! Would love to stay again "
United States
Matt W.
The price is AU$574
includes taxes & fees
29 Sept - 30 Sept
A soul soothing escape. Artistically built and lovingly maintained.
A room with a hexagonal glass ceiling, a bed with a plaid blanket, and a view of greenery outside.

6. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is AU$278
includes taxes & fees
27 Sept - 28 Sept
Floating Island Dome - Pet-Friendly Lake Retreat
A covered patio with a view of a lake, outdoor furniture, and a wooden deck.

7. Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
10.0 out of 10, Exceptional, (11 reviews)
"This property is so special! The setting is absolutely gorgeous and the home itself is perfect both inside and out. We stayed here for a college graduation and had multiple generations-the layout was terrific for all of us. We especially loved sitting by the lake, enjoying the views from the screened in porch, and family time in the game room. The communication from the host was excellent and the entire process from beginning to end was seamless. We hope to return for another stay!"
United States
Jennifer E.
The price is AU$1,308
includes taxes & fees
26 Oct - 27 Oct
Family's Paradise: 3BR/2BA,Game Room & Lake Access
A two-story house with a balcony, surrounded by trees and a grassy yard.

8. Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach

Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
Smithfield
10.0 out of 10, Exceptional, (3 reviews)
"Best vacation home ever!!! Host, property, and home met all of our families expections. Just perfect !"
United States
Dianne S.
The price is AU$1,240
includes taxes & fees
28 Sept - 29 Sept
Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
A large, two-story house with a well-lit front porch and multiple windows.

9. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is AU$602
includes taxes & fees
4 Oct - 5 Oct
Elizabeth Cottage
A cozy living room with a sofa, ottoman, and dining table with chairs. There are windows with curtains, a wooden ceiling, and a view of the outdoors.

10. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Canaan
9.8 out of 10, Exceptional, (8 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
The price is AU$613
includes taxes & fees
18 Oct - 19 Oct
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
A small, single-story house with a white exterior and a dark roof. It features a front door, two windows with shutters, and a small porch area.

11. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is AU$602
includes taxes & fees
4 Oct - 5 Oct
Nightingale Cottage
A wooden cabin with a dining table and chairs, a red recliner, and large windows overlooking a lake.

12. Lakefront Home w/ Dock & Sugarloaf Access on Scenic Porter Lake

Lakefront Home w/ Dock & Sugarloaf Access on Scenic Porter Lake
Strong
10.0 out of 10, Exceptional, (42 reviews)
"Pet friendly with a nice spot on the lake. Nice place with great views."
United States
Al Q.
The price is AU$405
includes taxes & fees
27 Sept - 28 Sept
Lakefront Home w/ Dock & Sugarloaf Access on Scenic Porter Lake
A two-story house with a red roof, located by a lake surrounded by dense green trees.

13. July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather

July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay"
United States
Michael Y.
The price is AU$1,254
includes taxes & fees
7 Oct - 8 Oct
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

14. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is AU$634
includes taxes & fees
3 Oct - 4 Oct
Once Upon a Time — A Peaceful Maine Escape
A wooden deck with wicker furniture, a television, and a view of a deck area with outdoor furniture.

15. Loon Lodge on Locke Pond: Relax, Recharge and Explore

Loon Lodge on Locke Pond: Relax, Recharge and Explore
Chesterville
10.0 out of 10, Exceptional, (2 reviews)
"L’emplacement est parfait beaucoup de belle commodité intérieur et extérieur. Petit point négatif les lits ne sont pas faites et et doit les laver avant de partir."
Canada
Anny
The price is AU$643
includes taxes & fees
13 Oct - 14 Oct
Loon Lodge on Locke Pond: Relax, Recharge and Explore
A wooden kitchen with a large window, a black countertop, and three bar stools.

16. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (3 reviews)
"Great for kids. Lots of space. Convenient location. Plenty to do locally or venture out to explore. Recommend renting the golf cart to get back and forth down the camp road to the dock.. water is clear and clean, rock bottom at shore. Fast response from host who lives close by."
United States
Melissa B.
The price is AU$981
includes taxes & fees
25 Oct - 26 Oct
Welcome to "the east Madison chapel"
A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

17. Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings

Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Wayne
10.0 out of 10, Exceptional, (1 review)
"The property was very nice!"
United States
James D.
The price is AU$1,436
includes taxes & fees
29 Sept - 30 Sept
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakland Hotel Reviews

Comfort Inn & Suites Wilton

Comfort Inn & Suites Wilton

10/10 Excellent
"Pet friendly was important and the hot tub plus breakfast were wonderful. I've stayed here 2 or 3 times and it's always been great."
Jeffrey 2-night trip
Posted 12 hours ago
Comfort Inn & Suites Wilton

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
127
Accommodation
151 Holiday Homes
Lowest Price
AU$209
Highest Price
AU$1,436